Glycoglycerolipids or glycolipids are a class of lipids found in nature. The compounds contain most frequently one or two monosaccharide units linked glycosidically to mono- or diacylglycerol. Glycolipids with three or four monosaccharide units are also known. They are especially important in higher plants, algae and bacteria where they are located in photosynthetic membranes, they are less pronounced in animals.
Glucoglycerolipids have physical as well as biological properties that make them an interesting component in food production, and several health-promoting properties have been reported, such as inhibition of tumour growth in the gastro intestinal tract (GIT), anti-inflammatory as well as antiviral effects: see Colombo, D, et al. Cancer Letters (Shannon, Ireland), (2000) 161, 201-205; Colombo, D., et al. Cancer Letters (Shannon, Ireland), (1998) 123, 233; Larsen, E., et al; J. Nat. Prod. (2003) 66, 994-995. Morimoto, A., et al. Phytochemistry, (1995) 40, 1433-1437; Nagatsu, A., et al. Bioorg. Med. Chem. Lett., 1994, 4, 1619-1622; Nakata, K. J. Biochem. (Tokyo), (2000), 127, 731-737; Pahlsson, P., et al. Arch. Biochem. Biophys. (2001) 396, 187-198; Shirahashi, H., et al. Chem. Pharm. Bull., 1996, 44, 1404-1406; Shirahashi, H., et al. Chem. Pharm. Bull., 1993, 41, 1664-1666; and Janwitayanuchit, W., et al, Phytochemistry (Elsevier), (2003), 64, 1253-1264.
Langworthy, T. A., et al. Biochimica et Biophysica Acta, (1976), 431, 550-569, describe the isolation of glucosamidyl glycolipids from an extreme thermoacidophile Bacillus acidocaldarius. The major compound, which comprises about 64% of the total lipids, appears to be a fatty N-acyl derivative of glucopyranosyl(1→4)glucosamine(1→3)-diacylglycerol. The amide-linked fatty acid was primarily branched heptadecanoic, but also 11-cyclohexylundecanoic or 13-cyclohexyltridecanoic acid. A minor product was tentatively identified as O-β-D-glucopyranosyl-(1→4)-O-2-acylamido-2-deoxy-β-D-glucopyranosylmonoacylglycerol.
In bacteria and algae a large number of glycolipids containing different sugar combinations have been reported. For example, 1-(O-β-glucosaminyl)-2,3-diglycerides have been identified in Bacillus megaterium: see Phizackerley, P. J. R., et al. Biochem. J., 1972, 126, 499. It constitutes about 5% of the total lipid glucosaminide in the organism and was separated from other lipids by chromatography. The lipid contained glycerol, fatty acids and glucosamine in the molar proportion 1:2:1. The fatty acids were bound by an ester linkage. Partial acid hydrolysis or alkaline hydrolysis of the lipid yields 1-(O-β-glucosaminyl)glycerol.
Shimizu, C. et al. Chem. Pharm. Bull. 1989, 37(8), 2258-2260 and Chem. Pharm. Bull. 1990, 38(12), 3347-3354, describe sialosylglycerol derivatives and their synthesis. In these compounds, an N-acylamino group is present in place of the hydroxyl group at the 4-position of the monosaccharide moiety (the point of attachment to the glycerol moiety being the 1-position).
JP 2-225489A describes glyceride derivatives having a monosaccharide group bonded at its 1-position to a glycerol moiety. These compounds also have an N-acylamino group in place of the hydroxyl group at the 4-position of the monosaccharide moiety.
Wu et al., Chin. J. Chem., 2008, 26, 1641-1646, describes the synthesis of natural α-6-dehydroxy-6-aminoglucoglycerolipids. The synthetic route involves the intermediate 3-O-(2′,3,4′-tri-O-benzyl-6-dehydroxy-6′-benzyloxycarbonylamino-α-D-glucopyranosyl)-1-O-palmitoylglycerol.
Fairweather, J. K. et al., Aust. J. Chem., 1998, 51, 471-482, describes the asymmetric dihydroxylation of alkenyl 2-acetylamino-2-deoxy-β-D-glucopyranosides. The synthetic route involves the intermediate (3′S)-4′-benzoyloxy-3′-hydroxybutyl 3,4,6-tri-O-acetyl-2-acetylamino-2-deoxy-β-glucoside.
DE 19634019 A1 describes glycoglycerolipids and their use as antimicrobials.
Anionic and cationic surface-active solutions are used in a number of applications such as detergents and emulsifiers.